


Second Best

by FollyOfWinchester



Series: Nothing Good Will Come [11]
Category: Supernatural
Genre: Anal Sex, Bottom Dean, Canon Compliant, Canon Het Relationship, Coda, Deleted Scenes, Dildos, Explicit Consent, Explicit Language, Explicit Sexual Content, F/M, First Time Bottoming, Headcanon, Implied Castiel/Dean Winchester, M/M, Missing Scene, Painful Sex, Pining, Season/Series 05 Spoilers, Season/Series 06 Spoilers, Strap-Ons, Vaginal Fingering
Language: English
Status: Completed
Published: 2014-02-22
Updated: 2014-02-22
Packaged: 2018-01-12 19:09:03
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,114
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1196211
Author URL: https://archiveofourown.org/users/FollyOfWinchester/pseuds/FollyOfWinchester
Summary: <blockquote class="userstuff">
              <p>Dean and Lisa try something new in the bedroom. Set during the Season 5 Coda.</p>
            </blockquote>





	Second Best

**Author's Note:**

> If you don't want to read any het, please feel free to skip this fic because it's by no means central to the plot. It's really just a Lisa/Dean fic where Castiel only comes up in Dean's thoughts.

Lisa blinks her eyes several times as a series of confused expressions cycle on her face. “You...want me to...what? Not that that doesn’t sound...interesting, but—”

“Fine. Forget it. Just forget I said anything! It was a stupid idea, anyway.” It really is a stupid idea. Dean knows it. He’d just be using her as a Cas replacement and that isn’t fair to either of them.

“Dean, what is going on with you? You’ve been brooding about something so just spit it out.”

He is NOT going to discuss this. What would he even say? _I’m brooding over the fact that I miss my angel pal’s dick, I jacked off in the garage in a super gay way to a memory of having sex with him, I saw...or maybe imagined some kind of spooky angel orgasm immediately after I jizzed all over myself, and then I prayed to him about it even though I promised myself I wouldn’t and he didn’t answer me anyway. Now I’d like you to fuck me in the ass so I can feel close to him again, please and thank you. Yeah. Right._ “It’s nothing. Seriously, just forget it.” He turns to storm off, but Lisa catches his shoulder.

Her face softens, “Wait, I’m sorry. I didn’t mean to shoot you down like that. I’ll just...let me think about it and I’ll get back to you. Um...how big would it need to be because I’ve got one already that might—”

“I don’t know! Fuck!” Dean can feel his face turning red, “I gotta go! Just forget it!!” _This is so goddamn embarrassing. She is never going to let me live this down. I feel like such a freaking idiot!_ He pushes past her and practically sprints to the kitchen for a beer.

~*~

It’s been a few weeks since his really freaking awkward discussion about anal sex and dildos with Lisa. In fact, after several days of feeling like a huge douchey idiot and beating himself up for even mentioning it in the first place, Dean had almost forgotten about it completely. Until tonight. 

After dropping Ben at a friend’s house for the evening, he and Lisa had gone out for dinner and a movie. As they walk up to the front door of Lisa’s house, Dean rests his hand on the small of her back and starts to run it down toward her hip. His fingers bump against some sort of thick strap under the fabric of her dress. _She must be wearing some heavy duty underwear or something. Oh man, is she riding the crimson tide this week? Damnit._ Puzzled, he looks over at her and she winks at him.

“Come on, I’ve got a surprise for you.” She grabs his hand and leads him directly to the bedroom.

 _Alright, so not that time of the month, then._ Dean wracks his brain trying to figure out what she could be planning, but his thought process is short circuited as she pushes him backward into the side of the bed. He leans up on his elbows as she unzips her dress, “I’m definitely liking this surprise so far.” The dress was tight up at Lisa’s chest, but hung more loosely around her waist and hips, so he hadn’t noticed anything surprising during their date. As Lisa slips the dress from her shoulders and it slides to the floor, Dean’s jaw drops. There are no panties to be found. In their place, Lisa is wearing what Dean can only think to describe as a “dildo holster.” _HOLY SHIT SHE REALLY BOUGHT ONE. AND SHE WAS WEARING IT ALL NIGHT._ His blood pressure skyrockets and he sputters out a series of incoherent noises as his brain tries desperately to catch up with exactly what is about to happen. She straddles him and unbuttons the first few buttons of his dress shirt while he stares dumbfounded up at her. 

Lisa finishes with his shirt and slides it off of his shoulders before leaning down and whispering into his ear, “I got everything we need, but you’re going to have to tell me what you want since I’ve definitely never done this before.” _HOLY SHIT HOLY SHIT HOLY SHIT._ She reaches over to the drawer of his nightstand and pulls out a dildo and a little bottle of lube. Dean’s eyes widen as the shock starts to give way to excitement and he can finally form a coherent thought. “Whoa.”

“What? Too big? Too small? Or do you hate the color pink? I didn’t want to ask you because it would have ruined the surprise, so I—”

“No, no. It’s...yeah...it’s good. It’s **really** fucking good.” Lisa had somehow managed to pick pretty much exactly what Dean had pictured in his mind when he first asked her about it. Maybe it isn’t exactly the right size and a little more pink than actual penis color, but it's been forever since he’s seen Cas’s dick anyway. Dean internally shrugs. _Close enough._ He’s suddenly conflicted between excitement and guilt. After all, she's doing this just for him, and here he is thinking about someone else. Not even a human someone else! _Holy shit, I can’t believe she was willing to put all this together for me._ As soon as Lisa finishes inserting and adjusting the surrogate dick into its holster, Dean cups her cheeks and pulls her into a sweet kiss, “Thanks, you’re awesome.”

“I know.” Lisa starts grinding against him and their kisses grow more passionate. Dean runs his hands down her neck and chest before massaging her breasts. She throws her head back at the touch and he leans in to suck on her nipples. She moans out his name and fists one hand in his hair while running her other hand over the breast that Dean isn’t lavishing with attention. His pants are starting to feel tight and he can feel her heat and wetness through the fabric. _She definitely deserves to get off before we give this strap-on thing a go._ He unbuckles his belt and lets Lisa lean up on her knees so he can slip his pants off. His dress shirt is still hanging from his forearms, so he tosses it aside before stroking the head of his cock along Lisa’s clitoris. She cries out in pleasure and pushes down onto him. He braces himself against the bed. The warmth and the pressure is perfect and he groans as she surrounds his cock inch by inch. Once she’s flush against him, she starts to move her hips again and he can feel the strap-on rubbing and slapping against his torso as a reminder of what they’re about to do. He times his upward thrusts with her movements and fingers her as much as he can underneath the strap-on gear. Soon she is panting and screaming his name and he knows she’s close. She starts to squeeze and pinch her own nipples and Dean has to look away because he’s close, too, but he doesn’t want to finish like this. Her movements stutter and she goes limp against him with a moan.

After a moment of recovery, Lisa leans back up and kisses along Dean’s jawline, “Ready?” _Hell yes I’m ready! I just wish Cas was... No! I’m with Lisa. Lisa is doing this for me. Shit, I am such an asshole..._ Dean nods almost imperceptibly as he struggles to push his guilt to the back of his mind. She lifts her hips up and he moans as she slides up his cock one last time. He’s so close. _Just gotta hold on a little longer._ She moves to stand between his legs, “So, how should we do this?” 

If he’s honest with himself, Dean kind of wants it to hurt, both because he knows he’s being a jerk to Lisa and because that’s how he imagines it would be with Cas, the new and improved fully charged angel of the lord. Cas probably wouldn’t be able to hold back and would roughly fuck him against the cold concrete floor of an abandoned warehouse after they’d cleared out a nest of demons. He’d be too sore to walk the next morning, but they’d blame it on the hunt if Bobby asked. _Hell yes! That’s what I need!_ Not sure how to ask for what he wants, Dean stammers out some vague instructions, “Just lube it up and go for it.” He slides his ass to the edge of the bed and looks up at Lisa’s perplexed expression.

“Are you sure? That seems like it would probably hurt...”

He tosses Lisa the bottle of lube and nods, “Don’t worry about it.”

She shrugs and coats the strap-on liberally before lining it up. Dean hears her mutter, “Alright, here goes nothing,” as she starts to press in.

Dean lets his arms slide out from under him and winces at the painful pressure as his head hits the mattress. It definitely hurts. There’s no danger of coming too soon now. Lisa grips Dean’s hips to steady herself as she continues to press forward. He squirms under her and twists his hands in the comforter.

“Dean, this doesn’t look very—”

No. This is exactly what he deserves. “It’s, ahh, no, it’s perfect. Keep going.”

“Are you sure about— Wha!” She lets out a yelp as Dean wraps his legs around her back and pulls her against him in one powerful movement. As her hips slap into him, he growls in pain, “Yes.”

Fuck, that hurt, but so does everything. His whole life is just one big pit of pain and regret. As the initial wave of searing sensation fades, he focuses on the feeling of having something other than his own fingers inside him. He closes his eyes and imagines Cas standing over him, Cas’s hands on his hips, Cas. A worried “Dean?” from Lisa snaps him back and he looks up to see a concerned look on her face. He unwraps his legs and attempts to reassure her. “See, hard part’s over. Now just, uh, pretend you’re me and I’m you and go to town.”

She smooths her hands over his hip bones and the lower part of his abs, “I don’t want to hurt you.”

“Seriously, it’s fine. I like it rough. Come on, haven’t you ever wanted to feel what it’s like to just fuck someone as hard as you can? I’m giving you permission!” _Fuck me like an angel. Fuck me like Cas would._

She straightens her shoulders and lets out a breath. “Alright. Just...please tell me if I _really_ hurt you, okay?”

Dean nods and closes his eyes as she braces herself on his hips again. She starts to move tentatively and then thrusts back in just barely. Dean pictures Cas, hair already sex mussed with that long lost necklace hanging from his neck. Another small thrust, and he remembers Cas letting every thought tumble out of his mouth as he had it, telling him how good everything feels and how much he wants Dean. He moans at the thought and bites his bottom lip to keep from letting Cas’s name slip. No way he wants to try and explain _that_ to Lisa. But the longing to see Cas again is overwhelming. He needs this fantasy, just a little longer.

His moaning must be giving Lisa more confidence that he actually does want to do this because her thrusts are getting more forceful. Yeah, that’s it. _Goddamnit, fuck me, Cas! Fuck me harder!_ He moans out, “Harder!” and Lisa is right there with him. The skin of her hips starts to make a slapping sound against his bare ass with each thrust. Spikes of pain mixed with pleasure jolt through his body and he twists his hands in the comforter again. “Yeah, fuck me harder!”

“God, Dean, you are **so** hard right now.” One of her hands leaves his hip and he opens his eyes to discover that rather than going for his cock, she’s fingering herself from behind. He groans into his own shoulder and shuts his eyes again. He’s honestly not sure how he feels about anything anymore, just that this is the hottest sex he has ever had in his whole fucking life. Lisa’s thrusts start to lose their rhythm. “Dean, again, I’m gonna—” Dean moans and imagines Cas’s cock throbbing inside him and filling him up and he can’t stand it. He grabs his own cock and comes in a few strokes with a shout.

“Cas!”

When he opens his eyes, Lisa’s panting above him with a frustrated look on her face. “Who’s Cas?”

_SON OF A BITCH._

~*~


End file.
